New approach to the synthesis of 2,3-dihydrofuro[2,3-b]pyridine derivatives: double reduction and double heterocyclization of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles in the presence of sodium borohydride

The reaction of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles with an excess of sodium borohydride resulted in diastereoselective formation of 2,3-diaryl-substituted 4,6-diamino-2,3-dihydrofuro[2,3-b]pyridine-5-carbonitriles. This process was accompanied by opening of the pyrrole ring in the starting compounds, followed by a double reduction and tandem closure of furan and pyridine rings.

This is a preview of subscription content, log in to check access.

Figure 1.

References

  1. 1.

    Fitch, R. W.; Spande, T. F.; Garraffo, H. M.; Yeh, H. J. C; Daly, J. W. J. Nat. Prod. 2010, 73, 331.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. 2.

    Zhou, Q.; Snider, B. B. Org. Lett. 2011, 13, 526.

    Article  CAS  PubMed  Google Scholar 

  3. 3.

    Gordon, J. C.; Phillips, E.; Gurley, D. A.; Heys, J. R.; Lazor, L. A.; Barthlow, H. G.; Mallamaci, M. A.; Keith, R. A. Eur. J. Pharmacol. 2010, 645, 63.

    Article  CAS  PubMed  Google Scholar 

  4. 4.

    Koike, T.; Hoashi, Y.; Takai, T.; Uchikawa, O. Tetrahedron Lett. 2011, 52, 3009.

    Article  CAS  Google Scholar 

  5. 5.

    Elmore, C. S.; Landvatter, S.; Dorff, P. N.; Powell, M. E.; Killick, D.; Blake, T.; Hall, J.; Heys, J. R.; Harding, J.; Urbanek, R.; Ernst, G. J. Labelled Compd. Radiopharm. 2014, 57, 342.

    Article  CAS  Google Scholar 

  6. 6.

    Bardasov, I. N.; Alekseeva, A. U.; Ershov, O. V.; Belikov, M. Yu. Tetrahedron Lett. 2015, 56, 5434.

    Article  CAS  Google Scholar 

  7. 7.

    Alekseeva, A. Yu.; Bardasov, I. N.; Mihailov, D. L.; Ershov, O. V. Russ. J. Org. Chem. 2017, 53, 1243. [Zh. Org. Khim. 2017, 53, 1227.]

  8. 8.

    Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Grishanov, D. A. Tetrahedron Lett. 2015, 56, 1830.

    Article  CAS  Google Scholar 

  9. 9.

    Ducker, J. W.; Williams, B. K. Aust. J. Chem. 1978, 31, 2327.

    Article  CAS  Google Scholar 

  10. 10.

    Belikov, M. Yu.; Fedoseev, S. V.; Ievlev, M. Yu.; Ershov, O. V. Chem. Heterocycl. Compd. 2017, 53, 1057. [Khim. Geterotsikl. Soedin. 2017, 53, 1057.]

  11. 11.

    Belikov, M. Yu.; Fedoseev, S. V.; Ershov, O. V.; Ievlev, M. Yu.; Tafeenko, V. A. Tetrahedron Lett. 2016, 57, 4101.

    Article  CAS  Google Scholar 

  12. 12.

    Zhu, D.; Ma, J.; Luo, K.; Fu, H.; Zhang, L.; Zhu, S. Angew. Chem. 2016, 128, 8592.

    Article  Google Scholar 

  13. 13.

    Zhang, J.; Zhang, J.; Kang, Y.; Shi, J.; Yao, C. Synlett 2016, 1587.

  14. 14.

    Kojima, T.; Kawajiri, I.; Nishida, J.-i.; Kitamura, C.; Kurata, H.; Tanaka, M.; Ikeda, H.; Kawase, T. Bull. Chem. Soc. Jpn. 2016, 89, 931.

    Article  CAS  Google Scholar 

  15. 15.

    Saleeb, M.; Mojica, S.; Eriksson, A.; Andersson, C. D.; Gylfe, Å.; Elofsson, M. Eur. J. Med. Chem. 2018, 143, 1077.

    Article  CAS  PubMed  Google Scholar 

  16. 16.

    Engler, T. A.; Gfesser, G. A.; Draney, B. W. J. Org. Chem. 1995, 60, 3700.

    Article  CAS  Google Scholar 

Download references

The reported study was funded by the Russian Foundation for Basic Research (according to the research project No. 16-33-60156 mol_a_dk).

Author information

Affiliations

Authors

Corresponding author

Correspondence to Mikhail Yu. Belikov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 447–450

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Belikov, M.Y., Fedoseev, S.V., Ievlev, M.Y. et al. New approach to the synthesis of 2,3-dihydrofuro[2,3-b]pyridine derivatives: double reduction and double heterocyclization of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles in the presence of sodium borohydride. Chem Heterocycl Comp 54, 447–450 (2018). https://doi.org/10.1007/s10593-018-2287-x

Download citation

Keywords

  • 2,3-dihydrofuro[2,3-b]pyridines
  • sodium borohydride
  • diastereoselectivity
  • reduction